The Chesapeake School
by junior-4323
Summary: AU Blacklist at boarding school. Almost all the characters will be in the story at some capacity, but the focus is Keenler.
1. Chapter 1

**A/N: Hey! This is my first Blacklist fic and it's a Keenler one. I have seen that there are some pretty popular high school Keenler fics out there right now that I and many others love but I have had this idea for a while and hope that it can give you all a different side of the characters as high schoolers. They're in boarding school in this one (a little inspiration came from the movie School Ties) and most of the main characters will be introduced by the end of the second chapter. The first chapter is mostly background on Ressler but also the beginning of the boarding school aspect of the story. Reviews are welcome. Enjoy!**

Allen Ressler was once a white collar attorney. He defended bankers, politicians, and about any rich person that could get themselves in legal trouble. He worked at the headquarters of a large firm in Washington D.C. where he also lived in a beautiful Georgetown brownstone with his wife Amy and son Donald. Unfortunately for the Resslers, after a bad year, Allen was laid off from his job and could only obtain a legal occupation two hours from his current office. The job was at a small legal office in the middle of a rural Virginia farming town.

Moving was hard on Donald as he had to leave behind his only friends: his travel baseball team. He was an excellent baseball player and his parents were planning on sending him to the best high school for both academics and sports, possibly giving him the opportunity to get recruited to play baseball at the college level as well. The school being a private high school and a solid hour and a half drive from the Resslers' new home, Donald's dreams of playing more competitive baseball were all but crushed.

"Dad, this isn't fair," Donald whined as they packed the car with some essentials. It was a simple station wagon–their previous car being a company owned BMW that Allen had to return to the firm after he was laid off.

"I know kiddo, but sometimes we have to make the best of the worst," Allen responded, "Maybe you'll make some friends when you play baseball for your new school."

Donald pouted, but didn't make a sassy retort because he knew the move was hard on his parents as well. Donald was pretty smart for a thirteen year old and he tried to be sensitive to those he respected, especially during rough times. For most of his life Donald had it easy.

Donald started to go back in the house to get some final boxes as Allen went to grab the last few pieces of mail that they would receive at their home in DC.

"Hey Donnie, wait up!" Allen called out.

"I hate when he calls me that," Donald said under his breath as he turned around. "What is it?"

"You got a letter from that great boarding school that Jason went to," Allen said. Jason grew up around the corner from the Resslers and he was a total science geek who got into CalTech, but the boarding school he went to also had well-rounded academics and a impaticuraly good baseball team. Donald could never imagine playing for them.

Allen handed the letter to Donald whose eyes lit up as he read further and further down the piece of paper.

"They want me to play baseball for them!" Donald said with excitement.

"Yep, and on a full scholarship," Allen responded glancing up at Amy who came to see what all the fuss was about.

"The Chesapeake School wants me to play baseball for them!" Donald said as his chest puffed up.

"Oh honey that's great. We'd miss having you around though," Amy said.

"I think it's a great opportunity for you Donnie," his father told him.

By the end of the car ride to middle-of-nowhere Virginia, the Resslers decided to send their young son Donald to The Chesapeake School.

* * *

The majority of the students at the Chesapeake School were all sons and daughters of wealthy businessmen, politicians, and doctors. There were kids who had two parents that worked white collar jobs like that of Allen Ressler.

Donald's mom Amy was a school teacher and although Allen used to joke about her moral superiority, the two combined salaries certainly did not make enough money to send Donald to a private school like Chesapeake without a substantial scholarship, especially once the family moved out of DC.

Donald often felt out of place at the Chesapeake School when he would meet new students. Sometimes he had to throw in the fact that his father was a lawyer to get some traction in conversations.

The first time Donald felt that he did not have to be fake or throw in a fact about his life before his family moved, was when he met Aram Mojtabai. Donald was not impressed at first, but after working his way through wannabe Kennedys he realized it was a good thing that Aram was a little more awkward and different from the typical Chesapeake student.

"Hey Aram," Donald said as they sat next together for lunch during the third week of school.

"Hey Ressler," Aram responded.

"You know you can call me Donald, Aram. It ain't a great name, but you don't have to be all formal or anything," Donald said.

"Oh, some of those guys over there were calling you Ressler," Aram told him while pointing to a group of three tall and broad shouldered boys, "I thought if they were, maybe I should too."

Ressler recognized them from baseball and waved at them. The boys looked at each other and snickered like gossipy middle schoolers. Ressler frowned but didn't think much of it.

Although the Chesapeake Eagles did not begin their official season until the spring, the team got together and began causal practices and workouts led by the seniors. Ressler got to know some of the other boys, most of whom were much larger and stronger in their physicality than Ressler, although none of them could run faster. Ressler was one of the fastest runners on his travel baseball team back in DC. His ability to put the ball in play and eye for fly balls made him a valuable leadoff hitter and center fielder.

"So Ressler, you excited for criminology next?" Aram asked tentatively, bringing Ressler out of his baseball daydream.

"Yeah, that class is really interesting," Ressler responded. Both Ressler and Aram were interested in investigation and crime, making a class taught by the excellent teacher Raymond Reddington all the more worthwhile.

Before Aram could get another sentence out, the bell rang signifying the end of freshman lunch.

Aram and Ressler got up to throw their trash away and stack their trays on top of the garbage can. They went out the doors of the old school dining room with long tables and high ceilings made of carved brown wood.

"The food is so much better than I expected it to be," Aram said. Aram mentioned how much he liked the food about twice a week, but Ressler agreed too much to tell Aram he got the point.

"Yeah, especially 'cause it's free," Ressler said.

Aram was the only other student that Ressler met that attended Chesapeake on a full scholarship. He scored highly on some programming test and got scholarship offers from his pick of boarding schools. Aram's family was more well off than the Resslers, but he was planning on going to a public school before he received his test results.

The passing bell rang a few seconds before Aram and Ressler turned the corner toward Mr. Reddington's class. They both sighed knowing that they would either get their heads chewed off or be the target of Mr. Reddington's sarcasm for the entire period.

The door creaked open before Ressler and Aram scattered to their seats in the last row. Mr. Reddington waited for them to sit down before he started class.

"Donald, Aram, I prefer it when my students arrive to class on time, especially when we have a new student," Mr. Reddington said, his glare pointed at Ressler.

Ressler was confused more than embarrassed by Mr. Reddington's statement. New students were usually not allowed to start at boarding schools in between the beginning of freshman and junior year.

I would like you all to welcome "Elizabeth Scott," Mr. Reddington said as he waved his hand for a girl with shoulder length brown hair and blue timid eyes to join him at the front of the room.

"Lizzie here had to start a few weeks late, none of which is your concern," Mr. Reddington continued, "Now, without out any fuss let's begin today's lesson.

Lizzie walked back and sat in the empty seat between Ressler and Aram in the back of the room.

"Hi, I'm Donald, but you can call me by my last name, Ressler," he introduced himself, "It's a better name anyways."

Lizzie laughed.

"You can call me Liz," she said will a smile before turning her attention back to Mr. Reddington.

 **A/N: Okay, I know I didn't get a lot of characters or plot in, but you'll see most of them by the end of chapter two . Thank you for getting through this chapter and leave some reviews if you would like, they would be greatly appreciated! I'm going to try and upload two to three chapters a week so I would expect the next one on Tuesday or Wednesday.**


	2. Chapter 2

**A/N: So it's still Wednesday where I am, sorry for the delay, but school papers come first. One quick note: I forgot that I would be eventually be including Tom in the story when I wrote the first chapter. In the first chapter, Liz was referred to as Elizabeth _Keen_ , but since then I have changed her last name to Scott as the show revealed. From now on that is her last name and just try to forget that she was ever a Keen when reading this story :-)! Enjoy chapter 2!**

Criminology was the last class of the day for Aram, Liz, and Ressler. The two boys showed Liz around the campus' colonial style buildings in which the architecture resembled that of a small liberal arts campus. After their impromptu tour, the boys led Liz back to the library to do homework and study. Ressler was so caught up in showing Liz around that he forgot about Audrey, the girl in his math and English classes that he had a crush on.

The library was divided into a lab style section and a traditional library. Aram was even impressed with the technology, but for basic homework and studying the three students opted to sit in the older section of the library that was had tall wooden bookcases and long study tables with green lamps.

"This place is incredible," Liz said, "I've never been to a high school that looked this cool before."

Ressler smiled at how giddy and high her voice was as they walked to a table. An upperclassmen who was studying shushed them, but Ressler just quietly laughed as he walked past the annoyed girl. Aram settled at an open table for four. Liz sat down next to Aram and Ressler sat across from Liz.

"So tell me about Chesapeake! I haven't met that many people yet," Liz tried to say under her breath, but her voice was still a bit loud for the library as a different student, a boy, turned around and glared at them.

"Well, there are a lot of kids like _that_ ," Ressler said in an effective whisper, "Stuck-up rich kids who don't know how good they have it."

Aram hesitantly nodded in agreement.

"So, what are you taking?" Aram asked.

"I'm in Geometry, Freshman English, and Social Studies," she said as Aram and Ressler nodded at the basics, "Also French, P.E., and Criminology obviously, my dad would be pissed if I didn't take one of Red's...I mean Mr. Reddington's classes," Liz spit out quickly.

She hoped neither of the boys would ask her about her slip up, but-

"Red? What's up with you and Red?" Ressler asked in a more skeptical tone than necessary.

Liz sighed.

"Well, hopefully this isn't social suicide...," Liz paused, "The reason I got into Chesapeake was because of my father's friendship with Mr. Reddington. I didn't know him when I was little, but as I got closer to high school my dad started to worry," Liz continued. She looked to find disapproval in Ressler and Aram's eyes, but the only thing there was curiosity.

"My dad didn't have enough money to send me to private school, but the public school in our neighborhood is really bad and after the first week of school, we both knew it wasn't going to work out. Last week, my dad came home from a late dinner and told me that his friend Red could help me out."

Ressler and Aram nodded in unison, understanding her circumstance.

"Look, I'm here for baseball, Aram's here because he did well on his programming test, and pretty much everyone else has rich parents that could afford to send them here," Ressler said.

"So does that mean I'll fit right in or stand right out?" Liz said in a joking matter, but deep down she was curious.

"We haven't figured that out yet, but..." Aram trailed off as he watched a girl confidently wave at him as she walked past their study table. Aram returned a shy movement of the hand.

Liz grinned.

"Who is that, Aram?" she said teasingly as Aram began to blush violently. Ressler joined in on the teasing by lightly pushing his shoulder.

Aram could not get words to form so Ressler spoke for him.

"That is Samar. The three of us met at welcome week and I have been trying to convince Aram that Samar isn't too cool for him," Ressler said. "I think he might finally believe me."

Liz laughed. She did not realize that she could make new friends this quickly, especially when arriving late to a boarding school.

* * *

Once the three new friends finished their homework in the library, they headed off to their dorm rooms to relax until dinner time. As they exited the library, they were noticed by a group of boys standing in a circle and talking. One of them spotted a flash of red hair leaving the library and pointed.

"Hey, it's Donald Ressler," the brown-haired boy wearing a crisp white shirt, red tie, and beige slacks said.

The boy walked over and clasped Ressler's hand to give him a pat on the back.

"Hey Ress, remember me?" the boy asked.

Ressler knew he was either a junior or senior on the baseball team who played middle-infield.

"Umm...sorry, I'm not great with names," Ressler said, trying to ease the nerves out of his voice. He needed as many allies as possible at this school.

"Keen, Tom Keen, from baseball," the boy said.

"Oh right! You play short?" Ressler asked.

"Well, I'm going to be the starting second baseman this year. Most of the starters are going to be seniors though, so you'd be a go to pinch runner," Tom said.

Ressler felt some condescendence in Tom's voice, but kept it to himself. He started to continue walking to the dorms as the conversation reached an awkward pause.

"I guess, I'll see you tomorrow at practice then, _Tom_ ," Ressler said with emphasis on the boy's name.

"Remember it's Keen frosh, see ya Ress," he responded.

Ressler made sure to walk quickly with his friends, who were standing watching the conversation, back to the dorm. Tom or Keen or whatever seemed like a nice guy, but Ressler sensed that something was off about him and didn't want to deal with him in his third week of high school. Ressler was blocking out Aram and Liz who were having a conversation of their own.

"That Tom guy is cute," Liz told Aram.

Liz's statement made Ressler pause for a second. Liz noticed how he was staring at them so she walked closer to Ressler to include him in their chat.

"You think you could get me an in with the baseball team Ressler?" Liz said jokingly.

"I'll see," Ressler said, trying to play it cool. He had never dealt with relationships before.

"Alright guys, I'm going to take a shower before dinner time," Ressler said, "It's Farm Fresh Friday, right?"

"Yeah, I'm so excited to try it!" Aram said.

Every day of the month featured a themed meal. Aram was excited to see what day could beat Taco Tuesday or last Friday's Fried Chicken Feast. Farm Fresh Friday supposedly means that all the dishes are made from the student farm. Many of the students that choose the science track take agricultural electives and can opt to work on the school farm. There was no night that Aram would pass up dinner though, regardless of the food that was served.

"Oh wait, Ressler!" Aram called out as Ressler started walking into the boys' dorm. He walked back toward Aram who was still standing next to Liz.

"Even though tomorrow is our first Saturday class, do you think we could watch some Netflix on my computer? We could hang out in one of the lounges, the three of us," Aram proposed.

"Yeah sure, as long as we don't stay up to late. I have math at 8:30," Ressler said in frustration. He forgot his least favorite fact about boarding school: Saturday classes.

Once Ressler went up to his dorm, Liz and Aram sat on a bench outside the building until dinner.

"Wow, it's so surreal to be here Aram," Liz said, "I never thought in a million years that I would end up at a boarding school."

"Yeah, me too," Aram said, "So, what else can you tell me about yourself?"

"Well, I'm from Nebraska. I run track. I…I don't know Aram, I'm really not that interesting," Liz said.

"Look at it this way: you're from Nebraska, but that's not who you are. Who you are beyond that? That is what Mr. Reddington asked us at the beginning of the school year, he's probably going to talk to you abou... it's just, we need to answer that question in our final essay, who are we beyond where we are from and what we do in our spare time," Aram said, "So for me, I'm into computers and programming, but it's because with technology we can help people, we can change the world, I can. I'm not good at sports, but I do other things that the future is still figuring out and I get to be a part of that now and when I grow up, hopefully."

"Wow, what do I say to that?" Liz asked sarcastically, she couldn't compare to Aram.

"Well, how are you gonna make a difference with what you have? That's the thing that Ressler doesn't seem to get...don't tell him that, Mr. Reddington said that about him in private," Aram explained, "He sees people as black and white based on their background."

"The students here are snobby rich for the most part, but as the future of America, we need to respect them and collaborate with them while we have the time. Some of them might even be nice," Aram said. He felt bad for kind of throwing Ressler under the bus behind his back, but Ressler needed to know that he could not live seeing the world and people as only good and bad.

"You figure into the fabric of this too, Liz. You're part of the future, so what do you have?" Aram asked.

Liz thought for a long moment. She knew she wanted to help people, but she didn't have the ability to help in the same way that Aram could. Liz is good at understanding others, but how can that be useful in the long run?

"Hey guys," Ressler said, dragging Liz out of her thoughts. Liz was momentarily distracted by his wet hair that was sticking to his forehead and a shade darker than his normal color.

"Ready for some food?"

Aram burst off of the bench and practically jumped next to Ressler who started walking toward the dining hall. Liz laughed and followed the two boys. She knew that even after a few hours of knowing each other, the three of them would have many stories to tell by the end of the school year.


	3. Chapter 3

**A/N: Sorry I haven't updated in a few days, but with school wrapping up in the following weeks I am probably only going to be able to post one or two new chapters a week. Sorry about the delay, but please enjoy! I made this chapter a little longer too! Please review if you have anything to say about the story, I would love to know what you all think of it!**

Once the three freshman entered the dining hall, Aram dashed to the front of the line, almost knocking over a few students as he grabbed a white plate for his meal. Ressler and Liz laughed and slowly followed wanting to grab their food as well.

After piling chicken, squash, and an assortment of fruit grown on the school farm onto their plates, Liz and Ressler walked along the far side of the dining hall until they spotted Aram who was saving one seat next to him and one on the other side. Liz and Ressler walked through the gaps between the tables. Once they reached Aram, Ressler snuck under the bench and long wood table to sit on the other side. Meanwhile, Liz plopped down next to Aram who immediately began eating once Ressler and Liz were seated.

"Wow, this chicken is so good," Aram said through a mouthful of food.

Ressler scrunched his nose and looked at Liz who gave a light-hearted laugh after missing the unpleasant sight.

"I'm really glad I met you guys," Liz said, "It would have been so embarrassing if I had to eat all by myself."

Ressler nodded. His sat by himself right next to a group of girls who had become fast friends on the first day of school. He hated how they glanced over at him, giving him disapproving looks throughout the meal. Thankfully, he met Aram the following day during the orientation activities and Ressler had someone to sit and eat with everyday.

"Yeah, I get what you mean," Ressler said.

The two exchanged smiles, something Aram would have noticed if he wasn't so distracted by his half-eaten plate of food. The three students were mostly silent as they ate, throwing in a few jokes and anecdotes from the day between bites.

After Aram, Liz, and Ressler returned their dishes, they exited the dining hall and headed back for the dorms.

"So, what do you guys want to watch tonight?" Aram asked.

"What are you talking about?" Liz said.

"Netflix, remember?" Aram reminded her.

"Oh right, what do you want to watch Ress?" Liz asked.

"Um, since I have to be up early I'd be down for an episode of something, I don't think I could sit through a whole movie," Ressler said. He had his damn Saturday class in the morning and baseball in the afternoon. It was going to be a long day after a long week and he needed to rest at least one night.

"How about Friday Night Lights?" Liz suggested to the boys, "I've only watched a few episodes, but maybe we could watch an episode or two every Friday, you know, get a taste of what real high school is like."

Ressler and Aram looked at each other and nodded. They usually watched some lame–in Ressler's opinion–comedy that Aram found buried in the genre lists on Netflix. Both of them would be happy for a change of pace by watching a T.V. show instead.

"Okay!" Aram said with excitement. "I'll grab my computer and meet you guys in the lounge."

Aram swiped his card at the dorm entrance, Liz and Ressler following behind him. Aram waived to the security guards as he walked toward the elevator while Ressler led Liz into the lounge area on the opposite side of the building. Blue couches with green and white pillows surrounded the open space layout. A few boys were watching Sports Center on the flat screen T.V. while a pair of girls and a pair of boys were playing a round of foosball in the gaming area which was decked out with an air hockey machine, a ping pong table, and a pool table. Liz was even more impressed than she was fifteen minutes earlier in the dining hall.

"They sure have everything a teenager could ever want," Liz said with a hint of sarcasm.

Despite the unnecessary privilege she saw bestowed upon students by the school, Liz would be lying if she said she wasn't excited to take advantage of the amenities.

In the corner of the room, next to the wall of computers was a little nook on the window sill. It had blue cushions that matched the rest of the room and a few pillows that were left on the ground next to it. Ressler led Liz to the nook and invited her to sit down next to him.

"And it's comfy too!" Liz said. Ressler laughed along with her growing excitement.

The distance and columns that reached the ceiling separated the nook from the more crowded and noisier areas of the room.

"Aram usually grams a chair to put his computer on and we sit on either side of corner," Ressler said right as Aram dragged a rolling chair from one of the computers, "Speak of the devil."

Aram laughed as he set up the first episode of Friday Night Lights to play.

The three all got situated before getting lost in the show. Liz was sitting next to Ressler, enjoying the episode, her head resting next to his against the glass window. They were so close their heads were almost touching. Ressler distracted himself from the episode a few times to glance over at Liz and recognize their proximity. He thought that Liz and him were just becoming good friends quickly. Besides, he already had a crush on Audrey, he couldn't have a crush on two girls at once, right?

Before he knew it, Ressler was watching Matt Saracen telling Coach Taylor that his eyes were wide open. Liz discreetly wiped a tear away as the episode began to wrap up. Once it was over, Aram announced he wanted to watch "just one more".

"Alright guys, I have a big day tomorrow so I'll catch you at lunch," Ressler said as he pushed himself off of the window sill to leave.

"See you tomorrow," Aram and Liz said in unison while paying closer attention to starting the next episode.

Ressler waved just in time for Liz to see as she looked up briefly from the computer. With her returned wave and smile he walked back to his dorm room on the third floor.

Ressler entered the dark room, only the edge of his desk illuminated by the light of the lamp that shone through the window. His roommate, some rich doctor's son from Massachusetts named Matt, was probably still in the library working. He was actually one of the nicer students that Ressler had met, but Ressler and Matt barely saw each other because Matt was always studying in the library with his friends. At least, that's what he tells Ressler.

It was getting late, about 11 p.m., by the time Ressler had taken a shower, brushed his teeth, and changed for bed. Matt was still gone, but Ressler wasn't going to wait up for him. He hopped on top of his loft style bed and slipped under the navy blue covers. All that Ressler could think about when he closed his eyes were the many smiles and glances Liz gave to him throughout the day. With that in mind, Ressler dozed into a peaceful sleep with a grin on his face.

* * *

The following morning, Ressler arose from his deep sleep when something fuzzy and round hit him in the face. He abruptly opened his eyes to see a bright green tennis ball contrasting his dark blue duvet in the morning sun.

"Wake up Ress! We have geometry in 15 minutes," Matt hollered from the open doorway before shutting the entrance to the dorm room loud enough to jolt Ressler out of bed.

Ressler hopped off of his bed to check his alarm clock on his desk. It read 8:16.

"Shit!" he blurted out.

Ressler forgot to set it in time to get ready for his 8:30 a.m. class. Ressler quickly dug through his closet to find a blue oxford shirt and his navy baseball jacket. He threw on his dirty slacks that he had worn all week. He was still quite confused on how to do his own laundry.

Ressler slid on a pair of tennis shoes, not bothering to tie them, just giving him enough time to use the restroom and grab a snack from the vending machine in the lobby.

Ressler's hustle got him to class by 8:27 a.m., just giving him enough time to chat with the girl that sat next to him, Audrey Bidwell.

"Hey Don," she welcomed with a smile.

"Hi Audrey," he responded, "Ready for Saturday class?"

"No, I got up past my alarm clock–it looks like you did too," she commented on his appearence of sweaty, mussed hair and crinkled clothes.

"Yeah, barely got myself together," Ressler said, "You did a nice job, though. I couldn't even tell."

"Oh, thank you Don," Audrey responded, "So want to hang out in town tomorrow since we finally have no class."

Don was speechless. The only people that had asked to spend time with him at Chesapeake were Aram, Matt that one time his friends had ditched him, and some of the baseball players for a get together at the beginning of the school year. It was the first time any girl, let alone his crush, had expressed interest in him outside of the classroom.

"Of course, that sounds fun," Ressler said with a smile, trying to subdue his excitement.

For the rest of math class, Ressler stole glances at Audrey when she wasn't looking. He would have to go to a tutor or ask Aram for help on his homework, because the entire lesson was a blur, his thoughts deviating between Audrey and blankly staring at the teacher to make her think he was paying attention.

Once the bell rang, Audrey grabbed Ressler's wrist.

"Meet me outside the girl's dorm at ten tomorrow morning," she said.

"See ya," he returned with a confident grin.

* * *

Ressler was happy for the remainder of the morning. He actually paid attention in his Spanish class and was excited to meet up with his friends for lunch.

"Hey Aram, how's your day been," Ressler asked.

"It's been alright, how about you?" Aram asked.

"Audrey Bidwell asked me to hang out with her tomorrow!" Ressler said, unable to contain his excitement.

"She did?" Aram exclaimed in amazement.

"Who is she and what did she do?" Liz asked as she sat down with her plate of food next to Ressler and across from Aram.

"Audrey Bidwell asked Ressler to go hang out tomorrow!" Aram said, "He's had a crush on her since the first week of school."

"You know the first week of school was only two weeks ago, Aram," Liz said with amusement while turning her attention to Ressler, "Well, I'm happy for you. It's got to be tough to work out that whole relationship and teenage angst thing in first few weeks of boarding school."

"Yeah, everything happening so quickly, anything could happen," Aram said.

Liz nodded in approval, but frowned in disappointment once Ressler looked away. She came to lunch directly from her French class that Audrey Bidwell was also enrolled in. The girl didn't talk about Ressler specifically, but she mentioned how her dream boyfriend would spend all the time he could with her. Knowing Ressler would become consumed with baseball in the spring, Liz was worried about what he was getting himself into. Also, there was a very tiny almost miniscule part of Liz that wanted Ressler to keep spending more time with her...and Aram as well of course.

* * *

After school ended, Ressler headed to the locker room located near the sports fields. He changed into his practice uniform consisting of a navy t-shirt with green lettering, grey pants, and green socks. He matched all of the other boys on the team, except they all had their pant legs rolled down to their ankles. Ressler still liked to go for the classic high sock look.

Ressler grabbed his equipment bag from his locker and headed out to the field to meet up with the rest of the team.

"Hey Keen," Ressler emphasized, finally getting Tom's name right as he walked passed the junior.

He finished filling up his water bottle from the cooler at the end of the dugout before slowly walking toward Ressler.

"Hey frosh," Tom responded, "You excited for your one day weekend tomorrow?"

"I am!" Ressler exclaimed, "I've got a date–or something or other."

His chest puffed up in pride, almost daring Tom to challenge him. There were no real issues between the two, but there was certainly tension in the air.

"With who?" Tom asked, seeming genuine, "That loser Aram and the new girl. Let me tell ya man, that is not even close to a date."

Ressler restrained himself from beating Tom's ass for insulting his friends, but he attempted to stay cool and collected.

"No, Audrey Bidwell," Ressler said with as much swagger as he could muster.

Tom surprisingly impressed, nodded his head for a few seconds, smiled, and slapped Ressler's back before heading out for the team warm-up jog. Ressler started to follow Tom and the rest of the team, but he heard someone yelling from the dugout.

"Ressler! Can I have a word?" Coach Harold Cooper yelled out.

Ressler turned on his heel and jogged back to the dugout to talk to Coach Cooper.

"Hey Coach, what's up?" Ressler asked.

"I just spoke with the athletic director about scholarship athletes," Cooper started. "I have been informed that you among a few other students must meet some requirements to retain your scholarship. While I am completely against this idea, I thought I should let you know so you aren't surprised, and not in a good way, in the middle of the season."

Ressler stared at Cooper nervously. He was just starting to adjust to the team and now he was having another curveball, per say, being thrown at him.

"If you want to keep your scholarship, you are going to have to make all-league honors. This means beating out some of your older teammates for a position and being one of the best players in that position in the entire league. I know you can do this because of your natural talent and work ethic, but you are going to have to put a lot of time into baseball if you want to renew that scholarship."

Ressler swallowed hard. This was going to be a long grueling year.

 **A/N: I know a lot of you want to see some real Keenler. There will be a bit of a time jump in between the end of this chapter and the beginning of the next chapter, but there relationship in this story is ultimately a slow burn. Please feel free to leave a review if you have the time, I hope you enjoyed this installment!**


	4. Chapter 4

**A/N: So I know it's been a real long time since I updated this story. I am so sorry for that. If you are interested in continuing to read it I would recommend that you re-read the previous chapters, even I had to and I wrote them. I can't make any promises but I hope to complete this story within the next few months. Enjoy!**

Donald Ressler practically leaped off the bed when he woke up the third Monday in March. The Baseball season had officially started. He already set out his clothes for school and his uniform the night before. Apparently opening day for spring sports was a big deal at The Chesapeake School. It started with the girls' softball game after school, followed by boys' tennis, and ending with the baseball nightcap under the lights. Ressler planned to make a stop at the baseball locker room before heading to class. He wanted to check the line-up, hopefully he was starting.

Ressler took his time to button his shirt and put on his blue and green striped tie that matched with the other varsity baseball players. He combed his red hair back and wore a white batting practice cap backwards on his head, following the long tradition of the varsity team.

"Hey Tom!" Ressler said as he approached the junior whose attention was focused on the white piece of paper taped to the wall.

"Hey man, your leading off in center today," Tom said as he searched for his name down the line-up card.

Ressler jumped in excitement and relief. The first part of his quest for a scholarship was complete.

"Ah, there I am," Tom said with a hint of disappointment. He was batting eighth in the order instead of second like he had hoped.

"Well, I'll see you at warm-ups kid," Tom said, refusing to look Ressler in the eye as he left for class. Ressler soon followed after him, but veered off toward the math and science building as he got to the heart of campus.

Ressler was about to enter his geometry class when a hand grabbed his wrist. He looked up at his girlfriend with a smile.

"Follow me," Audrey said mischievously.

Ressler officially asked Audrey to be his girlfriend after they got back from winter break. They had spent a lot of time together, but had never done anything physical or had gone out on a real date. The only unfortunate part of their relationship was that it meant less time spent with Liz and Aram. Ressler always studied with Audrey and ate lunch with her the majority of lunches during the week. Matt had began to spend more time with Ressler as well and the three of them would often play silly games after they finished their homework. Ressler had few meals with Liz and Aram and his only exception to spending nights with Audrey was watching _Friday Night Lights_ with Aram and Liz. He convinced them to only watch one or two episodes each week so their tradition wouldn't run out too quickly. He wanted at least one excuse to spend time with the two of them.

Audrey dragged him into an empty corridor where they could have a tiny bit of privacy.

"What are we doing?" Ressler asked, giggling as she pulled him behind a column with a bit of force.

"This," she whispered before lightly kissing him on the lips.

Ressler breathed in her strawberry scent, enjoying the light kisses that started to spread to his neck. Ressler quietly moaned into her soft brown hair. Audrey seemed innocent, but she knew what she was doing. She had been Ressler's first kiss back in February. It was kind of cliché, the kiss coming on Valentine's day after he gave her a stuffed teddy bear and a chocolate heart. Audrey returned the gesture with a deep kiss, but a few days later she brought up the subject in a joking way saying she didn't think she needed to give Ressler anything and that it was a lame, consumer driven holiday. Ressler laughed it off, but was a little hurt by her comment.

Audrey moved her hands up Ressler's chest, slightly tugging on his tie as his hands worked their way down Audrey's back, barely hovering over her waist.

"I wish we could continue this, but class starts in five minutes," Ressler whispered into her ear.

Audrey nodded, giving him one last kiss on the lips before straightening out his shirt and tie and wiping off a few smudges of lip gloss that got on Ressler's face and neck.

They smiled at each other before walking out of the corridor and back toward their class.

* * *

As much as Ressler loved spending time with Audrey, he was more excited for Mr. Reddington's criminology class than any of the classes that they shared. After lunch with Audrey, Ressler caught up to Liz and Aram as they made their way to class.

"Nice of you to join us!" Liz said sarcastically.

"Hey, he has a good reason," Aram said in Ressler's defense.

"Whatever," Liz said as Aram and Ressler began catching up, something they used to do at lunch. Liz left herself out of the conversation.

The three students arrived at class a few seconds before the bell rang, just in time to grab their usual seats. Reddington began the lesson soon after.

"Now I know you all are not yet thinking about finals," Reddington paused, waiting for the groans of numerous students to die down.

"But instead of giving a paper final this semester, I am going to be assigning all of you a long-term project that I think you'll enjoy," he continued. "In groups of four, you will act as either a task force or legal team. These are going to be groups of defense attorneys, cops, federal agents, prosecutors, and since there needs to be five teams, something that peaks my interest. Now find three other people to join, first people to form a group get first pick."

Liz momentarily got over her frustration with Ressler and quickly formed a group with him and Aram.

"Samar!" Liz yelled out, but Samar was already on her way over. The four students raised their hands signifying that they were the first team formed.

Red smiled and walked over to their group. They didn't need to have a conversation to know what type of group they wanted to form.

"Great so you guys will be the defense attorneys," Red said calmly.

"What are you talking about? You said first group gets to-" Ressler began complaining.

"Oh how easy it is to get your goat Donald," Reddington said with a chuckle. "I already have you guys down as federal agents."

…

The rest of class turned into a discussion on how each of the different teams work in real life, but before long the bell rang and the school day was over. Students began filing out of class, Samar, Ressler, and Aram, lagging behind while discussing their project. Liz organized her binders while she prepared a few questions in her head that she wanted to ask Red about the project.

"Donald, can I speak with you about something?" Red asked. Liz could hear a hint of concern in his voice and decided to discreetly watch from the back of the classroom.

"Sure, Mr. Reddington. What's up?" Ressler asked.

"Now I don't want for this to come off as inappropriate, but if you are having sex or planning on-"

"What the hell are you talking about?"

Liz perked up at Ressler's raised voice.

"Due to some conversation that I heard in one of my earlier classes, I just want to make sure that you are aware of-"

"You know what? You're delusional and you've got no clue what you're talking about? I'm sorry but I've got a baseball to worry about so I'm gonna go."

"Donald-"

"You should come to the game. It'll be much more worth your time than flinging false accusations about my personal life at me," Ressler said before storming out of the classroom.

Red stood in shock and sighed as his eyes landed on Liz who awkwardly began moving toward the door. She froze before exiting and turned to Red.

"Look, I'm annoyed with him right now, but even I think that was out of line. You should apologize," she said.

"He's not having sex," Red concluded. Liz laughed a little, but soon got confused.

"Then why did you ask him about it. I mean, I would have lashed out too. Even Aram...actually he's too nice, Aram's a bad example-"

"Because of Audrey. Lizzie, I asked him because of Audrey. Earlier I overheard her talking to her friend about how she had lost her virginity on Friday night. As much as I wish I could unhear that statement for multiple reasons, I couldn't imagine Ressler being ready enough to handle sex just yet and-"

"Wait, Friday? Are you sure she said Friday?" Liz questioned.

"Yes, why?"

"We watch _Friday Night Lights_ every Friday. I mean, I get where you are coming from with the whole 'he's not ready deal,' but between baseball and the show, I don't see how he possibly could have on Friday."

Red sighed.

"Does this mean she's cheating on him?" Liz asked.

"If Audrey wasn't making it up to impress her friends, then I would assume so. Look Lizzie, I am a teacher, I can't get involved this deeply in my students' personal lives. If you want to go investigate the situation for your friend, then that's your prerogative. My only wish is that you are extremely careful. A lot of people could get hurt if you're not."

Liz nodded her head and walked out of the room. Part of her felt terrible for Ressler, knowing that his girlfriend was probably cheating on him. However, part of her became even more frustrated with him that he would spend almost all of his free time with someone who treated him like that instead of spending it with her and Aram, people that truly cared about him and would never deliberately do something knowing that it would hurt him.

As she walked across the quad she accidentally walked into a boy. She thought it was Ressler for a second because he was wearing the same outfit. She looked up to find Tom Keen gazing down at her.

"Hey Liz," he said with a smile.

"Hey Tom," she said, returning the smile.

"You're lucky you're friends with Ressler," he said.

"Why's that?" Liz asked in confusion.

"The free tickets," Tom said.

"What free tickets?"

"To the baseball game. He got you tickets right?"

Liz shook her head.

"That's weird. Anyways, we each get to give two reserved tickets out for every home game. Usually they're giving to family for opening night, but Ressler said that his folks wouldn't be able to come until later in the season. He said he was going to give them to his friends instead."

"He never even told me that he got free tickets. I was going to go anyways to support him, but it pisses me off that he didn't even tell me he had free tickets."

"Well, if you still want to support the team, I can give you my extra. I was gonna give it to a buddy, but he's kinda a loser."

"That's very nice of you Tom. Thanks!" Liz said with a grin.

"My pleasure," he said in return as he dug the ticket stub from his pocket and gave it to her.

* * *

After they ate dinner in between the tennis match and the baseball game, Aram and Liz walked to the stadium. Apparently Aram wasn't given one of Ressler's tickets either so Liz agreed to split the price of one with him. They looked through the stands for a set of seats and found two right behind Matt and Audrey.

"We should go sit with them," Liz said.

"Why? I thought you didn't want to hang out with Audrey," Aram questioned.

"I don't, but maybe if we can handle spending time with them, than we can spend more time with Ressler," Liz suggested.

"Okay," Aram said in agreement.

* * *

"Hey Ress," Tom said as the baseball players got all of their equipment situated in the dugout.

"Yeah?" Ressler responded.

"You gave your tickets to Audrey and Matt, right?"

"Just like you suggested," Ressler said with a look of concern on his face.

 **A/N: Sorry for not updating in forever. I probably should stick to one-shots, but right now I have a good idea where this is going which I didn't have before. If you stuck with this story: THANK YOU SO MUCH! I really appreciate it! Unfortunately I wouldn't expect anything soon, but hopefully everything will slow down around the holidays. Thanks for reading!**


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